8-phenyl-1,4-dioxaspiro[4,5]decane-8-carboxaldehyde → HCID 22293589, compound

HRID 966977Notes

Reaction equation

HRID 966977 reaction equation
[C:1]1([C:7]2([CH:17]=[O:18])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]([Mg]Br)=[CH2:20]>>[CH:19]([CH:17]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:15][CH2:16]1)[OH:18])=[CH2:20]

Participants

3

Reactant 2

HCID 122302758-phenyl-1,4-dioxaspiro[4,5]decane-8-carboxaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 22293589HCID 22293589, compound

Procedure

Prepared from 8-phenyl-1,4-dioxaspiro[4.5]decane-8-carboxaldehyde (J. Med. Chem. 1975, 18, 593-599) and vinylmagnesium bromide according to the method of Description 22. 1H NMR (400 MHz, CDCl3) δ 1.31 (1H, br s), 1.42-1.69 (4H, m), 1.76-1.89 (2H, m), 2.23-2.28 (1H, m), 2.45-2.51 (1H, m), 3.85-3.96 (5H, m), 5.09-5.14 (2H, m), 5.55-5.63 (1H, m), and 7.21-7.39 (5H, m).

Sources & evidence

ORD record
ord-441f445707c842fb8e4e64e8cb4e2550
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

Loading…